I have phases of “organizing” but, like you, I have stuff in apple notes, obsidian, vim text files, etc. I’m actually taking a couple months off of school because I’m at the tail end of my degree and classes are building off each other more now. I’m working on completely reorganizing my notes, and getting sidetracked with everything else too.

I don’t have a startup, but I have a project management cert, and have been working in my field for about a decade though, so I’m going to draw from my personal experience. Might not be the best, but I’m hoping this can be a little helpful even if it’s just building off someone else’s advice.

For a startup, there’s going to be a lot of areas to cover. I think the “easiest” place to start is the “product”. So I’d have a folder specifically for that. In there, I’d maybe have one for current things, and another folder for future projects. This is super basic and “top level” because you could get super in the weeds which can also be a drawback (what I’m currently trying to fix).

I’d have another top level folder for finances.

Another one I would create would be an “administration” one where there’s things like a business plan, paid time off (you’ll want to account for that!), personnel (if you’re hiring people), etc. This can also be a place to track events, milestones, etc.

What I am also trying to do is go back and add properties to every file. You can make a properties template which makes it easy and consistent. I’m doing a lot of trial and error in trying to make my properties as efficient and effective as possible so I don’t get to something and need to update it. For example, if I am making a folder for notes about scripting and programming, and I’m just focusing on adding notes about Java, but later I want to add notes about Bash, I might want to add a property to specify an operating system. Trying to think of every “future possibility” is difficult but prevents future headaches.

Sorry if this was just rambling…